It is prepared from citric acid, which is first converted to itaconic anhydride by dehydration and decarboxylation. Itaconic acid anhydride is isomerized to citraconic anhydride, which is hydrolyzed and the resulting acid further isomerized under acid-catalysis to give mesaconic acid.[1]
Hydration of mesaconic acid, a conversion catalyzed by mesaconyl-C4-CoA hydratase, gives citramalic acid.[2]
The compound has been considered as a renewable precursor to the commodity chemical methacrylic acid.[6]
Referencesedit
^R. L. Shriner; S. G. Ford; L. J. Roll (1931). "Mesaconic Acid". Org. Synth. 11: 74. doi:10.15227/orgsyn.011.0074.
^Berg, Ivan A. (2011). "Ecological Aspects of the Distribution of Different Autotrophic CO 2 Fixation Pathways". Applied and Environmental Microbiology. 77 (6): 1925–1936. Bibcode:2011ApEnM..77.1925B. doi:10.1128/AEM.02473-10. PMC3067309. PMID 21216907.
^. Archived from the original on November 17, 2005. Retrieved September 8, 2005.
^"Barker, Horace Albert". The Stadtman Way: The Story of Two Biochemists at NIH. Office of NIH History. Retrieved December 21, 2011.
^Switzer, Robert L.; Stadtman, Earl R.; Stadtman, Thressa C. (2004). "H.A. Barker". Biographical Memoirs. 84. National Academies Press: 3–22. PMID 15484416. Retrieved December 21, 2011.
^Santosh K. Yadav; Kevin M. Schmalbach; Emre Kinaci; Joseph F. Stanzione III; Giuseppe R. Palmese (2018). "Recent advances in plant-based vinyl ester resins and reactive diluents". European Polymer Journal. 98: 199–215. doi:10.1016/j.eurpolymj.2017.11.002.
April 10, 2024
mesaconic, acid, several, isomeric, carboxylic, acids, obtained, from, citric, acid, colorless, solid, namespreferred, iupac, name, methylbut, enedioic, acididentifierscas, number, model, jsmol, interactive, image3dmet, b00338chebi, chebi, 16600, nchemspider, . Mesaconic acid is one of several isomeric carboxylic acids obtained from citric acid It is a colorless solid Mesaconic acid NamesPreferred IUPAC name 2E 2 Methylbut 2 enedioic acidIdentifiersCAS Number 498 24 8 Y3D model JSmol Interactive image3DMet B00338ChEBI CHEBI 16600 NChemSpider 10289044 NECHA InfoCard 100 007 146EC Number 207 859 2KEGG C01732 YPubChem CID 638129UNII 90UTM639KKCompTox Dashboard EPA DTXSID10883407InChI InChI 1S C5H6O4 c1 3 5 8 9 2 4 6 7 h2H 1H3 H 6 7 H 8 9 b3 2 NKey HNEGQIOMVPPMNR NSCUHMNNSA N NInChI 1 C5H6O4 c1 3 5 8 9 2 4 6 7 h2H 1H3 H 6 7 H 8 9 b3 2 Key HNEGQIOMVPPMNR NSCUHMNNBNSMILES OC C C C C O O OPropertiesChemical formula C5H6O4Molar mass 130 10 g molDensity 1 31 g cm3Melting point 204 to 205 C 399 to 401 F 477 to 478 K Boiling point 250 C 482 F 523 K decomposes HazardsGHS labelling PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P264 P271 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSynthesis and reactions editIt is prepared from citric acid which is first converted to itaconic anhydride by dehydration and decarboxylation Itaconic acid anhydride is isomerized to citraconic anhydride which is hydrolyzed and the resulting acid further isomerized under acid catalysis to give mesaconic acid 1 Hydration of mesaconic acid a conversion catalyzed by mesaconyl C4 CoA hydratase gives citramalic acid 2 History editThis acid was studied for the first time by Jacobus H van t Hoff in 1874 3 It was later shown to be produced by Clostridium tetanomorphum Further studies showed that this organic compound is involved in the biosynthesis of vitamin B12 It is a competitive inhibitor of fumarate reduction 4 5 The compound has been considered as a renewable precursor to the commodity chemical methacrylic acid 6 References edit R L Shriner S G Ford L J Roll 1931 Mesaconic Acid Org Synth 11 74 doi 10 15227 orgsyn 011 0074 Berg Ivan A 2011 Ecological Aspects of the Distribution of Different Autotrophic CO 2 Fixation Pathways Applied and Environmental Microbiology 77 6 1925 1936 Bibcode 2011ApEnM 77 1925B doi 10 1128 AEM 02473 10 PMC 3067309 PMID 21216907 Mesaconic acid Archived from the original on November 17 2005 Retrieved September 8 2005 Barker Horace Albert The Stadtman Way The Story of Two Biochemists at NIH Office of NIH History Retrieved December 21 2011 Switzer Robert L Stadtman Earl R Stadtman Thressa C 2004 H A Barker Biographical Memoirs 84 National Academies Press 3 22 PMID 15484416 Retrieved December 21 2011 Santosh K Yadav Kevin M Schmalbach Emre Kinaci Joseph F Stanzione III Giuseppe R Palmese 2018 Recent advances in plant based vinyl ester resins and reactive diluents European Polymer Journal 98 199 215 doi 10 1016 j eurpolymj 2017 11 002 Retrieved from https en wikipedia org w index php title Mesaconic acid amp oldid 1177056059, wikipedia, wiki, book, books, library,
